Sissy maids - the latest trend in relationships

 “Sissy Maids: The latest trend in relationships”

By Lolita Lankenstein

(as told to c.w. cobblestone)

Interview #1: Dawn, Mike and Tulip

Dawn and Mike snuggle on the sofa, the evening news muted on the big-screen TV. The amorous couple watches their sissy servant Tulip stoke the fire in the sprawling stone-hearth fireplace that dominates the ski lodge’s living room. Once the flame is sufficiently aroused, Tulip scampers to the kitchen and returns carrying three fresh hot toddies.

This would be a theme during my visit with the polyamorous trio: Dawn and Mike relaxed while Tulip, a man dressed as a woman, did all the work. If that seems strange, then you have not been introduced to the world of sissy maid cuckold relationships.

I hadn’t known about the lifestyle, either until last month, when my editor at CNS (Corundo News Service) handed me a novel assignment: Do a story about this burgeoning subset of the poly lifestyle. He explained that these sissy cuckold triads consist of a married couple and a male lover, although the unions differ from traditional threesomes, in that the three participants are not equal; the husband lives as basically a female slave to his wife and her lover.

Marching orders in hand, I began researching the story. It didn’t take long to track down Dawn, Mike and Todd — or, “Tulip”— who are open about their lifestyle on social media. I reached out to the trio on Facebook, and I Skyped with Dawn and Mike for a few minutes. Tulip was “on punishment,” they explained. I was dying to hear more, but figured it best to wait until I set up the interview, rather than waste possibly good material beforehand. They said they were heading to Colorado for a ski trip, and agreed to meet me in their massive Aspen ski lodge.

I was bursting with anticipation as I made the cross-country flight from CNS’s New York office. After a 45-minute Uber ride from the airport, I arrived at the lodge, which was tucked in a snowy ridge at the foot of the Rockies. Tulip answered the door, dressed in a plain, gray maid’s uniform. If I didn’t already know his background, I’d have never guessed he was a male. The sissy took my coat and introduced me to his wife and her lover. Dawn ordered him to tend to the fire and serve drinks. I eased into a chair across from the couple on the sofa and dug my digital recorder out of my bag.

Once Tulip served the hot toddies (none for him), he sat on the floor at Dawn and Mike’s feet. “He’s not allowed to sit on the furniture,” Dawn explained.

Everyone was settled in, so I pushed the red button on my recorder and began the interview:

CNS: So, thank you for allowing me into your life like this. Let’s start at the beginning: how did the three of you meet?

Dawn: So, Tulip and me were married for three years, and … well, we pretty much had a sexless marriage.

Mike: The little pansy can’t get it up.

Dawn (giggles): Don’t be mean, Mike.

Mike: Well, it’s true. He can’t get it up.

Dawn (sighs): No, he can’t. But at least he was honest about it when we first started dating, and he told me he didn’t mind if I saw other men; he just wanted a relationship with me. He also confessed that he was into crossdressing. Small, effeminate guys aren’t my thing, but with Tulip, I never had to worry about that, because I could be with the kind of men I’m attracted to, and he could do whatever he wanted to do as far as dressing in women’s clothes, as long as I didn’t have to see it — and as long as he kept paying the bills.

Mike: Tulip’s always been a sap for her.

Dawn (to Tulip): Aw, Master’s being mean again, isn’t he? It’s okay if my little Tu-Tu loves his mommy. Do you love your mommy, Tulip?

Tulip (clears his throat): Yes, Mistress.

Dawn: That’s my little baba. So, anyway, after a few dates, I knew Tulip wasn’t going to be much use in the sack, but he had a lot of other things going for him.

Mike (cups his hand over his mouth): Money.

Dawn: Oh, come on. It was more than that.

Mike: Money.

Dawn (laughs): Okay, so he makes a lot of money. But he was really sweet, too, and I found out early on that he had learned to make up for his … um, shortcomings with that tongue of his. We had it pierced. Show the nice lady, baba.

(Tulip sticks out his tongue, displaying three large studs)

Dawn: Those feel great on my toes. Best thing we ever did was getting our little Tulip pierced.

Mike (raises his finger): My idea.

Dawn (kisses him): Yes, it was.

CNS (to Dawn and Mike): So, how did you two meet?

Dawn: He was my personal trainer at the club. When he first started training me, he had a girlfriend, so there was never anything romantic there at first.

Mike: Not that I wasn’t attracted to her.

Dawn: Oh, God, yes! I thought he was hot from the minute I saw him; I mean, just look at him. Anyway, I had been dating around ever since I married Tulip, but at first, Mike was off-limits.

Mike: Until I broke up with Cheryl.

Dawn: Mmmm, that was the best news I’d ever heard, you breaking up with that bitch. When you mentioned it during our session, I wanted to jump your bones right then and there.

Mike: Oh, I’d been thinking that from the minute you signed up at the gym. But I’m not a cheater, and I was in a relationship with —

Dawn (sneers): With that stupid heifer.

Mike: Well, she’s long gone now. And I’m a one-woman man — and you’re my woman.

Dawn (snuggles closer to Mike): Mmmmm … you got that right.

CNS: So, you two started seeing each other —

Dawn: He made his move not long after he broke up with Cheryl. Of course, I wasn’t exactly hiding the fact that I wanted him to.

CNS: Did he know you were married at first?

Dawn: Oh, I had told him about Tulip even before he broke up with her.

CNS: What did you tell him?

Dawn: I told the truth: that my husband was a wimp crossdresser who couldn’t get it up, and that I had sex with other men. That Tulip worked all day and then came home and cleaned the house. That he was basically my maid, not my husband.

CNS (to Mike): How did that make you feel?

Mike: Shit, I thought it was sexy as hell. Made me want her even more, knowing her husband couldn’t have her.

CNS (to Dawn and Mike): Is it okay if I ask Todd a question?

Dawn: Oh, please call him Tulip. That’s his name now; we’re actually talking about getting it formally changed when we get home. But, go ahead; you can ask him anything,.

CNS (to Tulip): So, tell me about the first time you met Mike.

Tulip: Uh, my mistress had been talking about him for a long time, even before he broke up with his girlfriend, so I’d known about him for a while.

Dawn: I couldn’t shut up about my hot trainer, could I, Tu-Tu?

Tulip: No, Mistress.

CNS (to Tulip): What was your reaction when they started dating? When did you first meet him?

Tulip: Um, my Mistress had been dating Mr. Mike for a few weeks, and then she invited him home for dinner.

Dawn: I made Tulip clean the whole house, top to bottom. Then, I made him do it again.

CNS (to Tulip): Were you nervous?

Tulip: Yes, ma'am, very much so. I’d met my mistress’s boyfriends before, and that’s always nerve-wracking. But I knew from the way she’d been talking about Mr. Mike that he was different. She always made me clean the house when guys came over, but she never made me clean it twice.

CNS: And what did you think when you met him? I mean, he’s obviously built like a Greek god, and you’re … well, not to be mean, but you’re not.

Tulip: Uh, I know I’m inferior to my master, and so I’m glad my mistress has him to take care of her, because I … I can’t.

Dawn: No, Tulip, you can’t.

Mike (chuckled): Don’t worry, Tulip, I’ll pick up the slack.

CNS: So, when did you all decide to move in together and make this an official cuckold triad relationship?

Dawn: I mean, we fell in love. And Tulip has nothing to say about it. So, it kind of just happened.

Mike: We’d been talking about me moving in together for a while, and we finally had Tulip do it when we went to the Bahamas.

Dawn: Yeah, that was Tulip’s wedding anniversary gift: a trip to the Bahamas for my baby and me, and when we got back, Mike was all moved in — just like magic.

CNS (to Tulip): So, you paid for your wife and her boyfriend to go to the Bahamas, and you moved him into your home all by yourself? That must’ve been hard to deal with.

Tulip: Um, I’m just happy my mistress and master are happy.

Dawn: Go ahead, Tulip; speak freely. Was it hard when you had to move all Mike’s stuff into the house?

Tulip (bows his head): Yes, Mistress. It was very hard. It was one of the hardest things I’ve ever had to do. I felt like I was losing everything.

Mike: Quit whining, sissy, or I’ll take a switch to your ass.

Dawn (chuckles): Poor Tulip. I told you to answer and you get in trouble anyway. Can’t catch a break, can you?

Tulip: No, Mistress, thank you, Mistress.

CNS: By the way, that reminds me: When we Skyped last week, you said Tulip was ‘on punishment.’ What was that all about?

Mike: There were eggshells in my damn eggs, so I blistered his pansy ass.

Dawn: It’s one of Mike’s pet peeves, so he went to town with the cane.

CNS: Do you punish him often?

Dawn: Not as much as we did at first. Other than the occasional screw-up, like with Mike's eggs, Tulip’s learning how we like things done, so we don’t have to whip him as often.

Mike: Except when you ask me to whip him because it makes you horny.

CNS (to Dawn): It does?

Dawn: Oh, Gawd, yes. I swear, seeing my man beat him into a blubbering mess … to see him crying, and begging and pleading … and the sad, confused look on his poor little face, wondering why I had him whipped when he didn’t do anything wrong … yeah, it makes me horny. Like you wouldn’t believe.

CNS (to Tulip): That seems pretty unfair: You didn’t do anything wrong and you still get punished, after you work so hard to make life easy for them. Doesn't that bother you at all?

Tulip: I’m just here for my mistress and master to use however they want, and I appreciate it when they take the time to discipline me.

Dawn (to Tulip): Tell the reporter how you thank Mike for your punishment.

Tulip: Um … I … uh … I suck him.

CNS (to Tulip) You mean to tell me you have to give your wife’s boyfriend a blowjob to thank him for whipping you?

Tulip: Yes, Ma’am.

CNS: Wow. That's incredible. Okay, so, sex-wise, how does this work? Mike, are you bisexual? Do you and Tulip ever have sex?

Mike: I don’t know if you could say he’s actually having sex. Bill Clinton said a blowjob doesn’t count as sex, so I guess I’m safe.

CNS: So, Tulip, you don’t have sex at all, other than giving oral?

Tulip: Uh, no, giving my mistress and master pleasure is my sex life.

CNS: So, I assume you masturbate a whole lot, if you’re not getting any other action.

Mike: Oh, hell no. He only gets to cum once every few months. Otherwise, he gets lazy.

Dawn: And he runs his mouth after he’s cum, too. Tulip, tell the nice lady what your master did the last time we let you cum, and you gave me backtalk.

Tulip: Uh, Master gave me 50 with the cane and I had to sleep in the shed for a week.

Dawn (giggles): It gets cold out there, doesn’t it?

Tulip: Yes, Mistress.

Dawn: I’ve told you a million times: Don’t piss him off. (She snuggles her cheek into Mike's bicep). My baby is such a bad-ass.

CNS: Let’s back up. You said Tulip only cums once every few months? Seems hard to do; how do you know he’s not cheating and masturbating in the bathroom or something?

Dawn: Oh, I assumed you knew already. We have him caged.

Mike: Tulip, get up and lift your dress; show the nice reporter your cage.

(Tulip stands and hikes his dress, revealing a pink plastic tube covering what’s obviously a tiny penis).

CNS: Oh, my gawd! I’ve heard about these chastity devices, but I’ve never actually seen one. Isn’t that uncomfortable?

Mike: How the hell am I supposed to know? You wouldn’t catch me wearing something like that in a million years.

Dawn: That’s because you’re a real man, and he’s a little sissy.

CNS (to Tulip): Is it uncomfortable?

Tulip: Um, I’m used to it, but sometimes it does feel a little tight.

Mike: Good thing you can't get that little weenie up, ain't it? That would make it even tighter.

Tulip: Yes, sir.

CNS: So, what’s the living arrangements? Does Tulip have his own room?

Dawn: He sleeps on the floor down in the basement, in the laundry room.

Mike: If he’s good, we let him sleep on his little blanket.

Dawn: We go by the point system. If he screws up during the day, we give him points. Three points, no blanket.

Mike: Shells in my eggs? That was ten points.

Dawn: So, no blanket for three days.

CNS: And you make him sleep in the shed for the really bad infractions?

Dawn: That’s Mike’s thing. (giggles) He’s so bad.

Mike: Hey, sometimes you gotta let the little pansy know who’s boss. So, I put his ass in the shed for a few days.

Dawn: Or a week.

Mike: Yeah, when he really makes me mad.

CNS: Tulip, what's that like sleeping in the shed?

Tulip: I don't like it, ma'am, but my master knows what's best for me, and he sends me to the shed so I'll learn my lesson.

CNS: But what's it like?

Tulip: It's freezing in the winter, and in the summer the bugs eat you up. That's why I try hard to serve my mistress and master well, so they don't send me out there.

CNS: And then when you sleep in the shed, you’ve got to get up and go to work?

Tulip: Yes, ma’am.

CNS: And then you come home and do housework? That sounds like a long day. You must get tired.

Dawn: Sissies aren’t allowed to get tired. (Giggles) Although I admit, we do leave messes sometimes. The poor little pansy was up all night last Monday cleaning the wine stain out of the carpet, and then Mike kept him up until nearly 3 in the morning the next night polishing his Range Rover.

Mike: Hey, I was meeting my buds for some golf and I wanted my ride looking sharp. What’s the point in having a sissy around if you’ve got to worry that he might be a little tired.

CNS: Well, it’s getting late, so I’m going to wrap this up. It’s been fascinating, to say the least.

Dawn: Maybe you could find a little sissy maid of your own who’ll pay the bills and let you have a love life with a real man. It’s the best, believe me.

CNS: Well, I’m certainly tempted.

NEXT MONTH: My journey into the world of sissy cuckold triads continues with my interview with Kimberly, her lover, James, and their servant Daisy.

Until then, I’m your CNS roving reporter, Lolita Lankenstein

 

 

“Sissy Maids: The latest trend in relationships Part II”

By Lolita Lankenstein

Cornudo News Service Correspondent

(as told to c.w. cobblestone)

 

In the last edition of CNS Weekly, I discussed my visit with Dawn, Mike and Tulip, who introduced me to the world of sissy/cuckold triads. It was a moving experience which prompted me to dig deeper and learn more about this amazing lifestyle.

Next, I reached out to Kimberly and James. Through our brief emailed correspondence I learned they’re an interracial couple (she’s white, he’s black), and they own a sissy named Daisy. I didn’t have travel far from the Cornudo News Service’s New York offices for this leg of my journey; my interview subjects lived in a Manhattan high-rise. It’s a truly elegant space with a stunning view of the Chrysler Building, although the otherwise-luxuriant apartment had just a few pieces of furniture during my visit.

An emaciated maid whose lips were cartoonishly blown up with Botox answered the door. I felt a rush of female power as I gave the once-over to this mousy, androgenous servant who was curtseying to me. I drew a deep breath and smiled. This lifestyle was growing on me.

“Welcome,” the pathetic creature squeaked through those bubble lips. The maid peeked up at me with sad, saggy, dark-circled eyes, a sure sign that sleep-deprivation was a way of life for this sissy. “Please come in.”

Kimberly and James met me in the foyer smiling. I was surprised to see she was pregnant; they hadn’t mentioned that in their emails.

After niceties were exchanged, Kimberly nodded at her maid. “Daisy, take drink orders. Orange juice for me.”

Daisy curtsied in response to my request for a vodka spritz and scurried off to the kitchen.

James waved me toward a chair. “Sorry, most of the furniture’s gone. In a few days, we’re moving to a house in Rye now that we’re going to have two kids.”

I settled into the chair and fished my recorder from my bag. “Oh, do you already have a child?”

“Yes, Shondra; she’s sleeping in her crib,” he said, easing onto the couch next to his lady.

“She’s 15 months old,” Kimberly added.

When Daisy returned with the drinks, I noticed the baby monitor receiver clipped to his apron strap.

Kimberly snapped her fingers and pointed. “Take a break, Daisy, and come kneel over here. This nice lady wants to do an article about us.”

Daisy curtsied and complied. I pushed record.

***

CNS: So, tell me how you three came to this kind of relationship.

Kimberly: Well, once upon a time, this … thing was my husband, believe it or not. I was never happy, and cheated on him like crazy. Then James came into the picture.

CNS: What happened then?

Kim: Tell her what happened when James came into the picture, Daisy.

Daisy: Um, Master took over the household, Ma’am.

Kim: Well, duh, that’s obvious, you stupid sissy. Tell her what happened the night he stayed over the first time.

Daisy: Um, well … Mistress brought him home, and I started to whine about it, so … um, so my Master hit me.

Kim: No, actually, he did more than hit you. He kicked your little pansy ass.

James: (chuckling) Oh, come on, now, I just slapped the little sissy around a little bit. Had to establish the pecking order.

Kim: (snorts) As if that was ever in doubt. (turns to Daisy) Tell her what else James had you do that night.

Daisy: Uh, I had to stand in the corner with my hands on my head holding a dollar bill against the wall with my nose.

Kim: Tell her how long your master kept you there.

Daisy: A-a-all night, Ma’am.

CNS: Wow, and you kept your nose to the wall that whole time?

Daisy: Yes, Ma’am.

Kim: (giggles) It was kind of mean; when we finished in the bedroom, we forgot about the little sissy and fell asleep.

James: Oh, the little candy-ass was fine, weren’t you, Daisy?

Daisy: Yes, sir.

CNS: Daisy’s quite the little sissy. His lips sure are … full. Obviously a heavy Botox treatment. There’s a lot in there; does that hurt at all, Daisy? It looks painful.

Daisy: Um, yes, Ma’am, really it hurts when I smile.

James: But what did we tell you about that?

Daisy: (lowers eyes) Sissies have no reason to smile, sir.

James: Sissies have no reason to smile. Besides, I like how they look. Tell the nice reporter: what do we call those lips?

Daisy: (swallows hard) They’re your dick-sucking sissy whore’s lips, Master.

James: Damn skippy. I want my dick-sucking sissy whore’s lips to look like dick-sucking sissy whore’s lips. I don’t care if it hurts when you smile.

CNS (to Daisy) So, going back to the beginning of your marriage, when did you first tell Kimberly that you were into crossdressing?

Daisy: Well, um … Ma’am, I don’t mean to contradict you, but I never was into crossdressing.

James: (grins) That was my rule. When I moved in, I told him there was only gonna be one man in this house. So, I had Kim sissy him up.

Kim: He was already a skinny little wimp, so it didn’t take much work.

Daisy: (in response to the sound of a baby crying crackling through the speaker on his apron strap) May I please be excused?

Kim (nods at the sissy, who labors from his kneeling position and darts down the hall. He reappears moments later holding the crying baby.)

Daisy: Permission to change her, Ma’am?

Kim: Go ahead.

Daisy: Yes, Mistress. (lays a blanket on the living room floor before setting the baby on it and removing a shitty diaper)

CNS: She’s beautiful.

Kim: Thank you. We don’t let Daisy change her unless one of us is present.

CNS: I don’t blame you. But, wow, that’s got to be great to have a sissy around to change all the diapers.

Kim: Tell me about it. (crinkles her nose) I don’t do diapers.

James (grabbing Kimberly and hugging her) You shouldn’t have to. Your time should be spent pleasing me!

CNS: How does that work if you both are out? Who changes the diapers then?

Kim: Oh, if we go out, we just have James’ little sister Janae come babysit. Daisy hates it when Janae comes over.

Daisy: Um, ma’am, permission to put Miss Shondra back in her crib?

Kim: First, tell the reporter why you hate it so much when Janae babysits you.

Daisy: Um, Mistress, it’s an honor and privilege to serve Miss Janae—

Kim: Don’t give me that shit; tell the truth or I’ll have James whip the skin off that sissy little ass. Why do you hate it so much when Janae comes over to babysit you?

Daisy: (tears welling up) She … she’s really mean to me, Ma’am.

CNS: Mean? How so? Give me an example.

Daisy: Well, last time she came over, I was rubbing her feet, and she put the roach clip on my nose and kept trying to knock it off by flicking her toes at it.

CNS: Ow, poor sissy, I bet that hurt.

Daisy: Yes, Ma’am, it did.

CNS: What else does she do to you?

Daisy: She puts Ben Gay inside my cage.

CNS: Oooh, that IS mean. Poor little you.

Kim: Stop complaining, sissy, and put my daughter back in her crib. And then come refill these drinks. (points to my drink, most of which is gone) Look at that. How dare you let our guest’s drink get so low? (turns to James) Can you teach the little sissy a lesson after he puts Shondra to bed?

James: You got it. (winks at Daisy) Hurry back now. That candy ass is mine. I think maybe it’s time I give you another respect notice.

Daisy (face turns white) Y-yes, sir. (scurries down the hall with the baby in his arms)

CNS: Wow, whatever you said really scared the sissy. What’s a respect notice?

Kim: (chuckles) Just watch. You don’t mind if things get sexual, do you?

CNS: Hell no, girl. This article isn’t PG.

James: (guffawing) Well, what’s about to happen ain’t exactly R-rated, either.

(Daisy returns, head hung low, shoulders drooping. He kneels before James)

James: (nodding at his crotch) Come on, bitch.

(Daisy slinks forward, unzips James’s fly and pulls out his long dick. James slaps him upside the head, prompting him to start sucking. It takes only a minute for James to get hard, whereupon he slaps the sissy a second time, and Daisy stops fellating his master)

James (to Daisy) You know what to do, sissy.

(Daisy flips up his maid’s dress, shimmies down his fluffy panties and bends over the couch, a look of abject fear in his eyes. James walks up behind him and positions his dick)

James: Put this in your article. (shoves his dick in, causing Daisy to yelp) Sometimes the sissy gets lazy and needs to be taught a lesson. It was completely disrespectful to let a guest’s drink get low like that. And we have a way of dealing with disrespectful sissies, don’t we, sissy?

Daisy: (crying) Owww, y-yes, Master.

Kim: (to CNS) Isn’t it sexy watching the little pansy get put in his place like this?

CNS: Oh, gawd, yes. This is one of the hottest things I’ve ever seen.

Kim: He’ll be the meekest little sissy in the world when this is over. Won’t you, Daisy?

Daisy: (still openly bawling) Unngh, owww, y-yes, Mistress, please, Mistress.

James: (increases the ferocity of his humping, causing Daisy to cry harder): Ahhhhhhhhh!

(The battery light on my recorder flashed. Damn it, I forgot to change the batteries! I pushed stop.)

***

After James came, he threw Daisy onto the floor. The sissy landed with a thump, curled into the fetal position and began sobbing. It made me so horny to see the little sissy so utterly debased and defeated like that. It took the little pansy damn near 10 minutes before he could even move.

He finally got up and continued serving us. For the rest of the evening, my drink never got below the halfway point. And Daisy was indeed the most cowed, eager-to-please sissy I’d ever seen!

My visit ended after about three hours. I was now a cuckold/sissy maid triad junkie.

I needed to find out more.

And I did just that. But that’s a story for next week.

Until then, this is your roving CNS reporter Lolita Lankenstein signing off.